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EP1636319B1 - Preparations aqueuses de colorants stabilisees - Google Patents

Preparations aqueuses de colorants stabilisees Download PDF

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Publication number
EP1636319B1
EP1636319B1 EP04734214A EP04734214A EP1636319B1 EP 1636319 B1 EP1636319 B1 EP 1636319B1 EP 04734214 A EP04734214 A EP 04734214A EP 04734214 A EP04734214 A EP 04734214A EP 1636319 B1 EP1636319 B1 EP 1636319B1
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EP
European Patent Office
Prior art keywords
red
reactive
pigment
blue
direct
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP04734214A
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German (de)
English (en)
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EP1636319A1 (fr
Inventor
Klaus Saitmacher
Josef Geisenberger
Karl-Heinz Schweikart
Till Borchert
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Clariant Produkte Deutschland GmbH
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Clariant Produkte Deutschland GmbH
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Publication of EP1636319A1 publication Critical patent/EP1636319A1/fr
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents

Definitions

  • the invention relates to the field of colorants, in particular for use in recording liquids for writing and recording devices, e.g. for ink-jet printing process (ink-jet process).
  • ink-jet printing process ink-jet process
  • the ink-jet or ink-jet process is a contactless printing process in which droplets of the recording liquid are directed from one or more nozzles onto the substrate to be printed.
  • the recording liquids and the colorants contained therein must meet high requirements, in particular with regard to purity, freedom from particles, solubility, storage stability, viscosity, surface tension and conductivity.
  • the most important role is played by the dyes used in the inks. Although a large number of dyes have been developed, there are few that meet the demands of a modern ink-jet printing process. An important role is played by heavy metal complex colorants, in particular copper complex dyes and pigments. In addition to dye-based inks, increasingly pigmented inks are also being used in ink-jet printing.
  • biocide composition for aqueous heavy metal-containing colorant preparations and inks, which causes no precipitation.
  • biocide composition should protect the colorant preparations and inks in question in a wide pH range, in particular between pH 3 and 10, against microbial attack, since such colorant preparations are often marketed for reasons of stability in an acidic or in an alkaline medium on the market.
  • CMIT 5-chloro-2-methyl-4-isothiazolin-3-one
  • MIT 2-methyl-4-isothiazolin-3-one
  • bronopol 2-bromo-2- nitropropane-1,3-diol
  • the present invention therefore relates to the use of an antimicrobially effective amount of a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one and 2-bromo-2-nitropropane -1,3-diol as a biocide in aqueous colorant preparations according to claim 1, preferably water-containing recording liquids, in particular ink-jet inks having a heavy metal ion concentration of greater than or equal to 20 ppm, in particular greater than or equal to 50 ppm.
  • the upper limit of the heavy metal ion concentration should naturally not exceed the maximum concentration of the biocidal mixture.
  • the antimicrobial mixture can of course also be used in water-containing colorant preparations in which the problem of heavy metal precipitation does not exist or only to a small degree, eg at heavy metal ion concentrations below 20 ppm.
  • a content of 0.001 to 0.1 wt .-%, preferably 0.01 to 0.05 wt .-%, calculated as a solid and based on the total weight of the hydrous colorant preparation has proven to be expedient .
  • the quantitative ratio of the individual constituents CMIT: MIT: bronopol is preferably (0.005 to 0.1): (0.005 to 0.05): 1, in particular (0.03 to 0.065): (0.01 to 0.025): 1.
  • the antimicrobial mixture is usually in the form of a dilute, eg 5 to 15 wt .-%, aqueous solution, which may contain even small amounts of inorganic salts such as Mg nitrate and / or Mg chloride used.
  • the amount of this solution used in the colorant preparation is then preferably 0.01 to 1 wt .-%, in particular 0.1 to 0.2 wt .-%, based on the total weight of the colorant preparation.
  • colorants containing complexed heavy metals are colorants containing complexed heavy metals.
  • Suitable heavy metal complex colorants are reactive dyes, direct dyes, acid dyes, disperse dyes and pigments which contain a heavy metal complexed from the group consisting of Cu, Co, Ni, Fe, Cr and Al. Particularly preferred are Cu complex dyes and pigments.
  • Examples of such reactive dyes are CI Reactive Black 8, CI Reactive Black 31; CI Reactive Blue 7, CI Reactive Blue 14, CI Reactive Blue 21, CI Reactive Blue 28, CI Reactive Blue 38, CI Reactive Blue 82, CI Reactive Blue 89, CI Reactive Blue 158, CI Reactive Blue 182, CI Reactive Blue 190, CI Reactive Blue 203, CI Reactive Blue 216, CI Reactive Blue 220, CI Reactive Blue 244; CI Reactive Violet 1, CI Reactive Violet 5; CI Reactive Red 6, CI Reactive Red 23 and CI Reactive Brown 18.
  • Examples of direct dyes are CI Direct Blue 76, CI Direct Blue 84, CI Direct Blue 86, CI Direct Blue 87, CI Direct Blue 98, CI Direct Blue 199, CI Direct Blue 202, CI Direct Blue 290; CI Direct Black 112; CI Direct Brown 95 and CI Direct Violet 47.
  • Examples of acid dyes are CI Acid Blue 87, CI Acid Blue 185 and CI Acid Blue 249.
  • heavy metal complex pigments are CI Pigment Blue 15: 1-15: 4, CI Pigment Blue 17, CI Pigment Green 7, CI Pigment Green 37, CI Pigment Red 257, CI Pigment Red 271, CI Pigment Orange 65, CI Pigment Orange 68, CI Pigment Yellow 117, CI Pigment Yellow 129 and CI Pigment Yellow 153.
  • CI Direct Blue 199 (Cu complex)
  • CI Reactive Black 31 (Cu complex)
  • CI Reactive Black 8 (Cu / Co complex)
  • CI Reactive Red 23 (Cu complex).
  • Cu complex dyes are compounds of the following formulas (5c) to (5l).
  • M is preferably hydrogen and / or sodium, depending on the pH.
  • Suitable organic pigments which may be contaminated with heavy metal ions include monoazo, disazo, laked azo, ⁇ -naphthol, naphthol AS, benzimidazolone, disazo condensation, azo metal complex pigments, and polycyclic pigments such as phthalocyanine.
  • Suitable inorganic pigments which may be contaminated with heavy metal ions are, for example, titanium dioxides, zinc sulfides, iron oxides, chromium oxides, ultramarine, nickel or chromium antimony titanium oxides, cobalt oxides and bismuth vanadates.
  • organic pigments are carbon black pigments, such as gas or Furnaceruße; Monoazo and disazo pigments, in particular the Color Index Pigments Pigment Yellow 1, Pigment Yellow 3, Pigment Yellow 12, Pigment Yellow 13, Pigment Yellow 14, Pigment Yellow 16, Pigment Yellow 17, Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 81, Pigment Yellow® 83, Pigment Yellow® 87, Pigment Yellow® 97, Pigment Yellow® 111, Pigment Yellow® 126, Pigment Yellow® 127, Pigment Yellow® 128, Pigment Yellow TM 155, Pigment Yellow TM 174, Pigment Yellow TM 176, Pigment Yellow TM 191, Pigment Red 38, Pigment Red Pigment Red 214, Pigment Red 214, Pigment Red 214, Pigment Red 262, Pigment Red 266, Red Pigment 269, Pigment Red 274, Pigment Orange 13, Pigment Orange 34 or Pigment Brown 41; ⁇ -naphthol and naphthol AS pigments, in particular the Color Index Pigments Pigment Yellow 1, Pigment Yellow 3, Pig
  • the pigment is present in the form of finely divided particles, either alone or stabilized by dispersing aids, in the liquid medium.
  • the average particle diameter is preferably in the range from 1 to 1000 nm, particularly preferably in the range from 10 to 100 nm.
  • Pigments which can be stabilized without dispersing aids are known as self-dispersible pigments. These are usually surface-modified pigments whose surface has been modified by chemical processes such as sulfonation or diazotization and provided with functional, optionally charge-carrying groups or polymer chains (referred to in the English literature as self-dispersing or graft pigments).
  • Suitable dispersants are nonionic, amphoteric, cationic or anionic surfactants or polymers.
  • the present invention also provides aqueous colorant preparations, preferably recording liquids, in particular ink jet inks, containing 0.1 to 50 wt .-%, preferably 0.5 to 20 wt .-%, of at least one heavy metal complex colorant, 0.001 to 0 , 1 wt .-%, preferably 0.01 to 0.05 wt .-%, of said antimicrobial mixture, and 10 to 90 wt .-%, preferably 30 to 80 wt .-%, of deionized water, each based on the Total weight (100% by weight) of the colorant preparation.
  • aqueous colorant preparations preferably recording liquids, in particular ink jet inks, containing 0.1 to 50 wt .-%, preferably 0.5 to 20 wt .-%, of at least one heavy metal complex colorant, 0.001 to 0 , 1 wt .-%, preferably 0.01 to 0.05 wt .-%, of said anti
  • the present invention furthermore relates to aqueous colorant preparations, preferably recording liquids, in particular ink-jet inks, containing at least 20 ppm of heavy metal ions and 0.1 to 50% by weight, preferably 0.5 to 20% by weight, of at least one colorant 0.001 to 0.1% by weight, preferably 0.01 to 0.05% by weight, of said antimicrobial mixture and 10 to 90% by weight, preferably 30 to 80% by weight, of deionized water, respectively based on the total weight (100 wt .-%) of the colorant preparation.
  • aqueous colorant preparations preferably recording liquids, in particular ink-jet inks, containing at least 20 ppm of heavy metal ions and 0.1 to 50% by weight, preferably 0.5 to 20% by weight, of at least one colorant 0.001 to 0.1% by weight, preferably 0.01 to 0.05% by weight, of said antimicrobial mixture and 10 to 90% by weight, preferably 30 to 80% by weight, of deionized water, respectively based
  • Water used to make the recording liquids is preferably used in the form of distilled or demineralized water.
  • the colorant preparations according to the invention may additionally contain a shading colorant, preferably from the group C.I. Acid Yellow 17 and C.I. Acid Yellow 23; C.I. Direct Yellow 86, C.I. Direct Yellow 98 and C.I. Direct Yellow 132; C.I. Reactive Yellow 37; C.I. Pigment Yellow 17, C.I. Pigment Yellow 74, C.I. Pigment Yellow 83, C.I. Pigment Yellow 97, C.I. Pigment Yellow 120, C.I. Pigment Yellow 139, C.I. Pigment Yellow 151, C.I. Pigment Yellow 155 and C.I. Pigment Yellow 180; C.I. Direct Red 1, C.I. Direct Red 11, C.I.
  • Direct Red 37 C.I. Direct Red 62, C.I. Direct Red 75, C.I. Direct Red 81, C.I. Direct Red 87, C.I. Direct Red 89, C.I. Direct Red 95 and C.I. Direct Red 227; C.I. Acid Red 1, C.I. Acid Red 8, C.I. Acid Red 80, C.I. Acid Red 81, C.I. Acid Red 82, C.I. Acid Red 87, C.I. Acid Red 94, C.I. Acid Red 115, C.I. Acid Red 131, C.I. Acid red 144, C.I. Acid Red 152, C.I. Acid Red 154, C.I. Acid Red 186, C.I. Acid Red 245, C.I.
  • the shading colorant is preferably contained in an amount of 0.001 to 5% by weight, more preferably 0.01 to 1% by weight, based on the dry weight of the total colorants.
  • the colorant preparations according to the invention may also contain organic solvents, humectants, organic or inorganic bases or acids, cationic, anionic or nonionic surface-active substances (surfactants and wetting agents), and viscosity regulators, for example polyvinyl alcohol, cellulose derivatives or water-soluble natural or synthetic resins as film formers or binders for increasing the adhesion and abrasion resistance and light stabilizers in conventional amounts.
  • organic solvents for example polyvinyl alcohol, cellulose derivatives or water-soluble natural or synthetic resins as film formers or binders for increasing the adhesion and abrasion resistance and light stabilizers in conventional amounts.
  • Suitable humectants are, for example, formamide, urea, tetramethylurea, ⁇ -caprolactam, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, butylglycol, methylcellosolve, glycerol, N-methylpyrrolidone, 1,3-diethyl-2-imidazolidinone, thiodiglycol, sodium benzenesulphonate, Sodium toluenesulfonate, sodium xylenesulfonate, sodium cumene sulfonate, sodium dodecylsulfonate, sodium benzoate, sodium salicylate, and sodium butylmonoglycol sulfate.
  • Suitable solvents are, for example, monohydric or polyhydric alcohols, their ethers and esters, for example methanol, ethanol, propanol, isopropanol, butanol, isobutanol; dihydric or trihydric alcohols, in particular having 2 to 6 C atoms, for example ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, 1,2, 6-hexanetriol, glycerol, 2-ethyl-2-hydroxymethyl-1,3-propanediol, diethylene glycol, dipropylene glycol, triethylene glycol, polyethylene glycol, tripropylene glycol, polypropylene glycol; lower alkyl ethers of polyhydric alcohols, such as ethylene glycol mono-methyl, ethyl or butyl
  • the recording fluids for the ink-jet printing process may vary depending on the embodiment of this printing process, e.g. as continuous-jet, intermittent-jet, impulse-jet or compound-jet processes, still further additives, e.g. to buffer the pH, to adjust the electrical conductivity, the specific heat, the thermal expansion coefficient and the conductivity.
  • the colorant preparations of the invention can be prepared by mixing the said components in the form of dry powders, their solutions, water or solvent-moist presscake together.
  • the described colorants are prepared according to the stated requirements.
  • the dyes can be isolated from the initially obtained, preferably aqueous reaction mixtures by salting out and filtration or by spray drying, optionally after partial or complete desalting by means of membrane filtration.
  • the dyes may also be used as press cake (optionally also in flushing process) or as a powder.
  • the dye mixtures according to the invention in as salt-free form, i. free from NaCl or other common inorganic salts, which have arisen in the synthesis of the dyes used.
  • the procedure is preferably such that in a first step at least one pigment, either as a powder or as a press cake, optionally together with at least one dispersant, optionally with at least one organic solvent, optionally with at least one hydrotropic substance and optionally
  • the other additives are made into a paste in deionized water and then homogenized and predispersed using a dissolver or other suitable apparatus.
  • the fine dispersion is then carried out with the aid of a bead mill or another suitable dispersing unit, the fine dispersion or grinding taking place with cooling to the desired particle size distribution of the colorant, in particular pigment particles. Subsequent to the fine dispersion, the dispersion can be further diluted with deionized water.
  • the colorant preparations according to the invention can be used for dyeing and printing natural and synthetic fiber materials (eg polyester, silk, wool, blended fabric), in particular for recording text and Images can be used on different recording media, as well as for dyeing paper or pulp in the mass.
  • natural and synthetic fiber materials eg polyester, silk, wool, blended fabric
  • images can be used on different recording media, as well as for dyeing paper or pulp in the mass.
  • the recording fluids according to the invention are in the ranges suitable for ink jet processes. They deliver print images of high optical density with excellent light and water fastness.
  • the colorant preparations according to the invention are also suitable as colorants in electrophotographic toners and developers, such as one- or two-component powder toners (also called one- or two-component developers), magnetic toners, liquid toners, latextoners, polymerization toners and special toners.
  • electrophotographic toners and developers such as one- or two-component powder toners (also called one- or two-component developers), magnetic toners, liquid toners, latextoners, polymerization toners and special toners.
  • Typical toner binders are polymerization, polyaddition and polycondensation resins, such as styrene, styrene acrylate, styrene butadiene, acrylate, polyester, phenolic epoxy resins, polysulfones, polyurethanes, individually or in combination, as well as polyethylene and polypropylene, which contain other ingredients, such as charge control agents, waxes or flow aids, or may be subsequently modified with these additives.
  • resins such as styrene, styrene acrylate, styrene butadiene, acrylate, polyester, phenolic epoxy resins, polysulfones, polyurethanes, individually or in combination, as well as polyethylene and polypropylene, which contain other ingredients, such as charge control agents, waxes or flow aids, or may be subsequently modified with these additives.
  • colorant preparations according to the invention are suitable as colorants in powders and powder coatings, especially in triboelectrically or electrokinetically sprayable powder coatings, which are used for surface coating of objects made of, for example, metal, wood, plastic, glass, ceramic, concrete, textile material, paper or rubber.
  • powder coating resins typically epoxy resins, carboxyl- and hydroxyl-containing polyester resins, polyurethane and acrylic resins are used together with conventional curing agents. Combinations of resins are also used. For example, epoxy resins are frequently used in combination with polyester resins containing carboxyl and hydroxyl groups.
  • Typical hardener components are, for example, acid anhydrides, imidazoles and dicyandiamide and their derivatives, capped isocyanates, bisacylurethanes, phenolic and melamine resins, triglycidyl isocyanurates, oxazolines and dicarboxylic acids.
  • colorant preparations according to the invention are also suitable as colorants for color filters, both for additive and for subtractive color generation, and as colorants for electronic inks ("e-inks") or "electronic paper” (“e-inks”). paper”).
  • the antimicrobial mixture used according to the invention shows a high activity against a variety of common germs in a wide pH range. Even with prolonged storage occur no precipitations of heavy metal complexes of active ingredients.
  • parts are parts by weight.
  • the biocide mixture according to the invention does not form insoluble complexes with any of the heavy metal cations investigated.
  • the comparison biocides lead in the presence of Cu 2+ , Zn 2+ or Fe 3+ to a strong formation of precipitates.
  • the germ load was tested by determining the germ count on suitable culture media.
  • suitable culture media For the two control samples without biocide a strong germ growth was already detected after a few days, while in the dye solution with Biocidgemisch no viable microorganisms could be detected even after 5 weeks.
  • the pigment was, either as a powder or as a press cake, together with the dispersants, the organic solvent and the other additives in Dionized water and then homogenized with a dissolver and predispersed.
  • the subsequent fine dispersion was carried out with the aid of a bead mill, wherein the milling was carried out with cooling to the desired particle size distribution of the pigment particles.
  • the dispersion was then adjusted to the desired final pigment concentration with deionized water.
  • Pigment Blue 15 3 2.5 parts Acrylate resin, Na salt (dispersant) 1.2 parts Polyethylene glycol alkyl ether, Na salt (dispersant) 0.018 parts 2-Bromo-2-nitropropane-1,3-diol 0.0011 parts 5-chloro-2-methyl-4-isothiazolin-3-one 0.00037 parts 2-methyl-4-isothiazolin-3-one 0.0018 parts magnesium nitrate 0.001 parts magnesium chloride rest E-Water
  • Example 4 was repeated except that on the contrary the biocide was omitted to give the following composition: 20 parts Pigment Yellow 155 2.5 parts Acrylate resin, Na salt (dispersant) 1.2 parts Polyethylene glycol alkyl ether, Na salt (dispersant) rest E-Water

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Cosmetics (AREA)

Claims (8)

  1. Utilisation d'une quantité antimicrobienne efficace d'un mélange de 5-chloro-2-méthyl-4-isothiazolin-3-one, 2-méthyl-4-isothiazolin-3-one et 2-bromo-2-nitropropane-1,3-diol comme biocide dans des préparations aqueuses de colorants, qui présentent une concentration en ions de métaux lourds supérieure ou égale à 20 ppm, et dans laquelle le colorant est un colorant réactif, un colorant direct, un colorant acide, un colorant de dispersion ou un pigment, et contient, lié à un complexe, un métal lourd du groupe de Cu, Co, Ni, Fe, Cr et Al.
  2. Utilisation selon la revendication 1, caractérisée en ce que la préparation de colorant est un liquide d'enregistrement, en particulier en encre pour jet d'encre.
  3. Utilisation selon la revendication 1 ou 2, caractérisée en ce que la quantité antimicrobienne efficace est de 0,001 à 0,1 % en poids, de préférence de 0,02 % en poids, calculée sous forme de matière solide et par rapport au poids total de la préparation de colorant.
  4. Utilisation selon au moins l'une des revendications 1 à 3, caractérisée en ce que le rapport en quantité des constituants individuels 5-chloro-2-méthyl-4-isothiazolin-3-one, 2-méthyl-4-isothiazolin-3-one et 2-bromo-2-nitropropane-1,3-diol est de (0,005 à 0,1):(0,005 à 0,05):1.
  5. Utilisation selon la revendication 5, caractérisée en ce que le colorant est C.I. Reactive Black 8, C.I. Reactive Black 31, C.I. Reactivé Blue 7, C.I. Reactive Blue 14, C.I. Reactive Blue 21, C.I. Reactive Blue 28, C.I. Reactive Blue 38, C.I. Reactive Blue 82, C.I. Reactive Blue 89, C.I. Reactive Blue 158, C.I. Reactive Blue 182, C.I. Reactive Blue 190, C.I. Reactive Blue 203, C.I. Reactive Blue 216, C.I. Reactive Blue 220, C.I. Reactive Blue 244, C.I. Reactive Violet 1, C.I. Reactive Violet 5, C.I. Reactive Red 6, C.I. Reactive Red 23, C.I. Reactive Brown 18, C.I. Direct Blue 76, C.I. Direct Blue 84, C.I. Direct Blue 86, C.I. Direct Blue 87, C.I. Direct Blue 98, C.I. Direct Blue 199, C.I. Direct Blue 202, C.I. Direct Blue 290, C.I. Direct Black 112, C.I. Direct Brown 95, C.I. Direct Violet 47, C.I. Acid Blue 87, C.I. Acid Blue 185, C.I. Acid Blue 249, C.I. Pigment Blue 15:1-15:4, C.I. Pigment Blue 17, C.I. Pigment Green 7, C.I. Pigment Green 37, C.I. Pigment Red 257, C.I. Pigment Red 271, C.I. Pigment Orange 65, C.I. Pigment Orange 68, C.I. Pigment Yellow 117, C.I. Pigment Yellow 129 ou C.I. Pigment Yellow 153.
  6. Préparation aqueuse de colorant, contenant 0,1 à 50 % en poids d'au moins un complexe de métal lourd-colorant, 0,001 à 0,1 % en poids d'un mélange antimicrobien selon une ou plusieurs des revendications 1 à 4 et 10 à 90 % en poids d'eau désionisée, respectivement par rapport au poids total (100 % en poids) de la préparation de colorant.
  7. Préparation aqueuse de colorant, contenant au moins 20 ppm d'ions de métaux lourds, et 0,1 à 50 % en poids d'au moins un colorant, 0,001 à 0,1 % en poids d'un mélange antimicrobien selon une ou plusieurs des revendications 1 à 4, et 10 à 90 % en poids d'eau désionisée, respectivement par rapport au poids total (100 % en poids) de la préparation de colorant.
  8. Préparation de colorant selon la revendication 6 ou 7, contenant un colorant de nuançage du groupe C.I. Acid Yellow 17 et C.I. Acid Yellow 23 ; C.I. Direct Yellow 86, C.I. Direct Yellow 98 et C.I. Direct Yellow 132; C.I. Reactive Yellow 37; C.I. Pigment Yellow 17, C.I. Pigment Yellow 74, C.I. Pigment Yellow 83, C.I. Pigment Yellow 97, C.I. Pigment Yellow 120, C.I. Pigment Yellow 139, C.I. Pigment Yellow 151, C.I. Pigment Yellow 155 et C.I. Pigment Yellow 180; C.I. Direct Red 1, C.I. Direct Red 11, C.I. Direct Red 37, C.I. Direct Red 62, C.I. Direct Red 75, C.I. Direct Red 81, C.I. Direct Red 87, C.I. Direct Red 89, C.I. Direct Red 95 et C.I. Direct Red 227; C.I. Acid Red 1, C.I. Acid Red 8, C.I. Acid Red 80, C.I. Acid Red 81, C.I. Acid Red 82, C.I. Acid Red 87, C.I. Acid Red 94, C.I. Acid Red 115, C.I. Acid Red 131, C.I. Acid Red 144, C.I. Acid Red 152, C.I. Acid Red 154, C.I. Acid Red 186, C.I. Acid Red 245, C.I. Acid Red 249 und C.I. Acid Red 289; C.I. Reactive Red 21, C.I. Reactive Red 22, C.I. Reactive Red 23, C.I. Reactive Red 35, C.I. Reactive Red 63, C.I. Reactive Red 106, C.I. Reactive Red 107, C.I. Reactive Red 112, C.I. Reactive Red 113, C.I. Reactive Red 114, C.I. Reactive Red 126, C.I. Reactive Red 127, C.I. Reactive Red 128, C.I. Reactive Red 129, C.I. Reactive Red 130, C.I. Reactive Red 131, C.I. Reactive Red 137, C.I. Reactive Red 160, C.I. Reactive Red 161, C.I. Reactive Red 174 et C.I. Reactive Red 180; C.I. Pigment Red 122, C.I. Pigment Red 176, C.I. Pigment Red 184, C.I. Pigment Red 185 et C.I. Pigment Red 269 ; C.I. Direct Blue 199; C.I. Acid Blue 9 et C.I. Pigment Blue 15:1-15:4 en une quantité de 0,001 à 5 % en poids, en particulier de 0,01 bis 1 % en poids, par rapport au poids sec du colorant total.
EP04734214A 2003-06-11 2004-05-21 Preparations aqueuses de colorants stabilisees Expired - Lifetime EP1636319B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10326210A DE10326210A1 (de) 2003-06-11 2003-06-11 Stabilisierte wasserhaltige Farbmittelpräparationen
PCT/EP2004/005458 WO2004108841A1 (fr) 2003-06-11 2004-05-21 Preparations aqueuses de colorants stabilisees

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EP1636319A1 EP1636319A1 (fr) 2006-03-22
EP1636319B1 true EP1636319B1 (fr) 2007-04-25

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US (1) US20060127272A1 (fr)
EP (1) EP1636319B1 (fr)
JP (1) JP2006527218A (fr)
KR (1) KR20060017642A (fr)
CN (1) CN100560661C (fr)
AT (1) ATE360667T1 (fr)
CA (1) CA2528859A1 (fr)
DE (2) DE10326210A1 (fr)
ES (1) ES2284014T3 (fr)
WO (1) WO2004108841A1 (fr)

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JP5296296B2 (ja) * 2006-02-16 2013-09-25 ブラザー工業株式会社 インクジェット記録用インク
JP5296295B2 (ja) * 2006-02-16 2013-09-25 ブラザー工業株式会社 インクジェット記録用インク
JP5242013B2 (ja) * 2006-02-16 2013-07-24 ブラザー工業株式会社 インクジェット記録用インク
JP5296306B2 (ja) * 2006-09-19 2013-09-25 ブラザー工業株式会社 インクジェット記録用インク
JP5296305B2 (ja) * 2006-09-19 2013-09-25 ブラザー工業株式会社 インクジェット記録用インク
KR100863482B1 (ko) * 2008-01-02 2008-10-16 주식회사 컴베이스 이미지 재현 기기의 토너 이송용 롤러 재생을 위한 코팅 조성물
PL2272348T3 (pl) 2009-07-07 2015-08-31 Lanxess Deutschland Gmbh Kompozycje biobójcze
US8586272B2 (en) * 2009-07-28 2013-11-19 Xerox Corporation Toner compositions
US8933134B2 (en) 2010-06-09 2015-01-13 L'oreal Compositions containing agar and a softening agent
AT516549B1 (de) * 2014-11-20 2017-05-15 Wenatex Forschung - Entw - Produktion Gmbh Antimikrobielles Mittel zum biociden Ausrüsten von Polymeren
US11116217B2 (en) 2016-04-05 2021-09-14 Thor Gmbh Synergistic biocidal compositions containing 5-chloro-2-methylisothiazolin-3-one
CN109418262A (zh) * 2017-08-29 2019-03-05 三博生化科技（上海）有限公司 一种防腐剂及其制备方法
CN109221175A (zh) * 2018-09-30 2019-01-18 高菠 一种水稻恶苗病杀菌剂组合物及制备方法
CN111134136A (zh) * 2019-12-14 2020-05-12 嘉兴沃特泰科环保科技股份有限公司 一种ro非氧化粘泥控制及杀菌剂及其制备方法和应用
CN113956680B (zh) * 2021-11-24 2023-09-22 浙江纳美新材料股份有限公司 一种净味水油通用色精及其制备方法
CN114716845A (zh) * 2022-02-25 2022-07-08 青岛英杰泰新材料有限公司 一种酸性喷墨数码印花墨水、制备方法及应用
CN116005472B (zh) * 2022-05-25 2023-10-27 浙江天台锦豪印花材料有限公司 水溶性升华转印花油墨及其制备方法

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CN1236542A (zh) * 1999-05-04 1999-12-01 王兴民 异噻唑啉酮衍生物的应用
EP1122286A4 (fr) * 1999-06-09 2003-07-30 Seiko Epson Corp Encre pour impression a jet d'encre et son procede de production, jeu d'encres pour impression a jet d'encre et cartouche d'encre
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DE10326210A1 (de) 2004-12-30
US20060127272A1 (en) 2006-06-15
DE502004003623D1 (de) 2007-06-06
JP2006527218A (ja) 2006-11-30
CN100560661C (zh) 2009-11-18
ATE360667T1 (de) 2007-05-15
KR20060017642A (ko) 2006-02-24
EP1636319A1 (fr) 2006-03-22
WO2004108841A1 (fr) 2004-12-16
CN1806021A (zh) 2006-07-19
CA2528859A1 (fr) 2004-12-16
ES2284014T3 (es) 2007-11-01

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